IP Library Granted Patent US 8,466,206
Granted Patent B1
US 8,466,206 · App. 13/334,199 · Granted Jun 18, 2013

Process for preparing porous polymer particles

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Quick Facts
Patent No.
US 8,466,206
App. No.
13/334,199
Granted
Jun 18, 2013
Kind
B1
Abstract

A process for forming polymer particles with aligned pores and controlled narrow particle size distribution, including: a) forming an oil phase by dissolving a polymeric binder in a solvent; b) dispersing the oil phase into a water phase containing a controlled amount of particulate stabilizer and forming an oil-in-water emulsion of controlled narrow dispersed oil phase droplet size distribution; c) freezing the emulsion to freeze solvent in the oil droplets to form frozen solvent domains within the polymeric binder, and also the water in the continuous water phase; and d) removing the frozen solvent from the polymeric binder and the frozen water in the continuous water phase, thereby forming porous polymer particles of controlled narrow particle size distribution and containing directional aligned non-spherical pore structures. Optionally, the porous particles may contain encapsulated functional ingredients.

Claims (23)

1. A process for forming polymer particles with aligned pores and controlled narrow particle size distribution, comprising:

a) forming an oil phase by dissolving a polymeric binder in a solvent;

b) dispersing the oil phase into a water phase containing a controlled amount of particulate stabilizer and forming an oil-in-water emulsion of controlled narrow dispersed oil phase droplet size distribution;

c) freezing the emulsion to freeze solvent in the oil droplets to form frozen solvent domains within the polymeric binder, and also the water in the continuous water phase; and

d) removing the frozen solvent from the polymeric binder and the frozen water in the continuous water phase, thereby forming porous polymer particles of controlled narrow particle size distribution and containing directional aligned non-spherical pore structures, wherein the formed porous particles have a volume based particle size geometric standard deviation of less than 1.5 for particle size of the particles measured in equivalent circular diameter.

2. The process according to claim 1 , wherein the formed porous particles have a volume based particle size geometric standard deviation of less than 1.4 for particle size of the particles measured in equivalent circular diameter.

3. The process according to claim 1 , wherein the formed porous particles have a volume based particle size geometric standard deviation of less than 1.3 for particle size of the particles measured in equivalent circular diameter.

4. The process according to claim 1 , wherein the frozen solvent and water are removed from the frozen emulsion under conditions of reduced pressure.

5. The process according to claim 1 , wherein the polymeric binder comprises a copolymer resin derived from styrene and acrylic monomers, or a polyester resin.

6. The process according to claim 1 , wherein the polymeric binder has a concentration of about 5% to about 50% by weight in the oil phase.

7. The process according to claim 1 , wherein the solvent is dimethyl carbonate.

8. The process according to claim 1 , wherein the porous particles formed have a volume based mean particle size of 2 to 100 micrometers for particle size of the particles measured in equivalent circular diameter.

9. The process according to claim 8 , wherein the porous particles formed have a non-spherical shape characterized by a mean aspect ratio of 0.9 or less.

10. The process according to claim 1 , wherein the emulsion is frozen in liquid nitrogen.

11. The process according to claim 1 , wherein the removal of the solvent and water is achieved under vacuum with a controlled temperature ramp from −40° C. to 10° C.

12. The process according to claim 1 , further comprising including metallic flakes in the oil phase, and wherein the metallic flakes are encapsulated in the formed porous polymer particles.

13. The process according to claim 12 , wherein the metallic flakes are substantially 2-dimensional particles, having opposed main surfaces separated by a relatively minor thickness dimension, and have a main surface equivalent circular diameter primarily in the range of from about 2 microns to about 20 microns, and an aspect ratio of at least 2.

14. The process according to claim 12 , wherein the metallic flakes are present at a concentration of from about 3% to about 30% by weight relative to that of the total weight of solids.

15. The process according to claim 1 , wherein the ratio of water phase to oil phase is 1.5 to 5 by weight.

16. The process according to claim 1 , wherein the particulate stabilizer is an inorganic particulate stabilizer.

17. The process according to claim 16 , wherein the particulate stabilizer is colloidal silica.

18. The process according to claim 1 , wherein the porous particles formed have a porosity of at least 10 volume %.

19. The process according to claim 1 , wherein the porous particles formed have a porosity of greater than 50 volume %.

Assignments (14)
NOTICE OF SECURITY INTERESTS Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 056984/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0233 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056733/0681 →
RELEASE OF SECURITY INTEREST Recorded Jan 24, 2020
From: BARCLAYS BANK PLC
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST) INC.; KODAK AMERICAS LTD.; KODAK REALTY INC.; LASER PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES LTD.; NPEC INC.
Reel/Frame 052773/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 30, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; PFC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 049901/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 22, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: QUALEX, INC.; EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 050239/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (ABL) Recorded Sep 5, 2013
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
To: BANK OF AMERICA N.A., AS AGENT
Reel/Frame 031162/0117 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (SECOND LIEN) Recorded Sep 5, 2013
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 031159/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (FIRST LIEN) Recorded Sep 5, 2013
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC; KODAK AMERICAS, LTD.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE
Reel/Frame 031158/0001 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Sep 5, 2013
From: CITICORP NORTH AMERICA, INC., AS SENIOR DIP AGENT; WILMINGTON TRUST, NATIONAL ASSOCIATION, AS JUNIOR DIP AGENT
To: EASTMAN KODAK COMPANY; PAKON, INC.
Reel/Frame 031157/0451 →
PATENT SECURITY AGREEMENT Recorded Apr 1, 2013
From: EASTMAN KODAK COMPANY; PAKON, INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS AGENT
Reel/Frame 030122/0235 →
SECURITY INTEREST Recorded Feb 21, 2012
From: EASTMAN KODAK COMPANY; PAKON, INC.
To: CITICORP NORTH AMERICA, INC., AS AGENT
Reel/Frame 028201/0420 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 22, 2011
From: YANG, XIQIANG; BENNETT, JAMES R.
To: EASTMAN KODAK COMPANY
Reel/Frame 027431/0758 →